1,3-Dibromopropane → 2-[4-(3-Bromopropoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 657527노트

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HRID 657527 반응식
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.C([O-])([O-])=O.[K+].[K+].[Br:23][CH2:24][CH2:25][CH2:26]Br>CC#N>[Br:23][CH2:24][CH2:25][CH2:26][O:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

생성물 1

HCID 441197642-[4-(3-Bromopropoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane수율 86.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (CAS #269409-70-3) (10.5 g, 47 mmol) was dissolved in dry CH3CN (200 mL) and dry, pulverized K2CO3 (10.4 g, 75 mmol) was introduced. 1,3-dibromopropane (38.1 mL, 375 mmol) was added dropwise, and the reaction mixture was heated at 70° C. for 7 h under a nitrogen atmosphere. The cooled reaction mixture was filtered and the filtrate was evaporated to an oily residue, which was applied to a column of silica gel. Elution initially with hexanes, gradually increasing polarity to a mixture of hexanes/ethyl acetate (25:1, 20:1 and 10:1) as eluent, provided the title compound (13.93 g, 86%) which crystallized on standing to a white solid, m.p. 62-65° C.

후처리

  1. customdry
  2. additionwas introduced
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customthe filtrate was evaporated to an oily residue, which
  6. washElution initially with hexanes
  7. temperaturegradually increasing polarity
  8. additionto a mixture of hexanes/ethyl acetate (25:1, 20:1 and 10:1) as eluent

출처 및 근거

ORD 기록
ord-4c7e820adb7641b0bc25cf47346d48be
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076331B2

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